There is no better time in American professional soccer than the MLS Cup Playoffs. Just as the leaves begin to fall across the continent, the best 18 teams from the regular season make their way to the legacy-defining knockout tournament.
To win it all, the least amount of games a team has to play is five, before lifting MLS Cup—and only in the best-of-three series in the first round, can a side afford to lose a match in any manner.
For the clubs that finished eighth and ninth in their respective conference, there’s an additional hurdle to pass. They have to win the single-knockout wild card game, played midweek after the intensity of Decision Day and before the first round.
After a dramatic end to the 2025 regular season, we’ve got our matchups as the Portland Timbers host Real Salt Lake in the Western Conference, and the Eastern Conference sees Chicago Fire—in their first MLS Cup playoff appearance since 2017—battle Orlando City SC.
The Western Conference winner goes on to face San Diego FC, while the Eastern Conference winner sets up a series with the Philadelphia Union.
Here’s how Sports Illustrated sees the wild card round unfolding.
MLS Cup Western Conference Wild Card: Portland Timbers vs. Real Salt Lake
- Location: Portland, OR
- Stadium: Providence Park
- Date: Wednesday, Oct. 22
- Kick-Off Time: 10:30 p.m. ET / 7:30 p.m. PT
- How to Watch: Apple TV
The Portland Timbers are back in the wild card match for the second year in a row, and will hope to avoid the disaster that was a 5–0 loss to the Vancouver Whitecaps in 2024.
The Oregon side enters the postseason in poor form, with just one win in their last 10 matches.
Should they find success, it will likely rely upon Designated Players David da Costa and Kristoffer Velde, as well as Antony in midfield and Kevin Kelsey up top. The trio have been the difference makers this season, with Antony leading the way with a mere seven goals.
Head coach Phil Neville’s biggest question could come in the net. His preferred starter, James Pantemis, has struggled as of late. He has another Canadian international option on the bench in Maxime Crépeau, who has a reputation for standing out in big games.
For Real Salt Lake, all eyes turn to U.S. men’s national team midfielder Diego Luna and summer signing Victor Olatunji, who scored a brace in the Decision Day draw with St. Louis CITY SC.
Luna can be the game-changer and will look to continue the form that saw him score nine goals and provide seven assists.
While the Timbers are at home and have better goals-per-match and goals-conceded-per-match stat lines, their poor form and tactical decisions could cost them.
Score Prediction: Portland Timbers 1–3 Real Salt Lake
MLS Cup Eastern Conference Wild Card: Chicago Fire vs. Orlando City SC
- Location: Bridgeview, IL
- Stadium: SeatGeek Stadium
- Date: Wednesday, Oct. 22
- Kick-Off Time: 7:30 p.m. ET / 4:30 p.m. PT
- How to Watch: Apple TV
Chicago are back in the MLS Cup playoffs for the first time since 2017 when German legend Bastian Schweinsteiger was in midfield.
The Fire will host the match at SeatGeek Stadium—their former permanent home—despite primarily playing at Soldier Field this season.
Gregg Berhalter’s side leans on the potent attacking duo of striker Hugo Cuypers, who scored 17 goals, and MLS Newcomer of the Year contender, Philip Zinckernagel.
While they were purely reliant on those two early in the season, they have since shored up the backline, adding Canadian international Joel Waterman from CF Montréal in a late-season trade, elevating a defense which already featured standout center back Jack Elliott.
Form-wise, Berhalter’s side enters the clash on a five-game unbeaten run. Across their last 13 games, the Fire have just two losses.
Their opponent, Orlando City SC, had a chance to finish in the top four in the final weeks of the season, but squandered their opportunity by winning just once in their final seven games.
Óscar Pareja will turn to stars Martín Ojeda and Marco Pašalić in attack, as well as Peruvian international goalkeeper Pedro Gallese and USMNT fullback Alex Freeman at the back., to make a difference.
Ultimately, as Orlando has shown this season, playing on the road and amid poor form could cost them an early postseason exit in the Wild Card round.
Score Prediction: Chicago Fire FC 3–2 Orlando City SC
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This article was originally published on www.si.com as Predicting the 2025 MLS Cup Playoffs Wild Card Matches.